Synthesis of allylic amide functionalized 2H-chromenes and coumarins using a one-pot overman rearrangement and gold(I)-catalyzed hydroarylation

Sharif, S. A.I., Calder, E. D.D., Harkiss, A., Maduro, M. and Sutherland, A. (2016) Synthesis of allylic amide functionalized 2H-chromenes and coumarins using a one-pot overman rearrangement and gold(I)-catalyzed hydroarylation. Journal of Organic Chemistry, 81(20), pp. 9810-9819. (doi:10.1021/acs.joc.6b01881) (PMID:27680202)

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Abstract

A four-step synthesis of allylic trichloroacetimidates bearing a 2-proparyloxyaryl group has been developed from readily available 2-hydroxybenzaldehydes, and these have been used for the preparation of allylic amide derived 2H-chromenes using an Overman rearrangement and a 6-endo-dig hydroarylation. High yields of the 2H-chromenes were achieved using a stepwise approach involving an Overman rearrangement under thermal conditions followed by a hydroarylation reaction with a gold(I) triflimide catalyst. An alternative method where both reactions were performed as a one-pot process was also developed and instead used a gold(I) chloride catalyst activated by silver(I) hexafluoroantimonate for the cycloisomerization step. The allylic amide derived 2H-chromenes were converted to the corresponding coumarin analogues by a pyridinium dichromate (PDC)-mediated chemoselective allylic oxidation.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sutherland, Dr Andrew and Harkiss, Mr Alexander
Authors: Sharif, S. A.I., Calder, E. D.D., Harkiss, A., Maduro, M., and Sutherland, A.
College/School:College of Medical Veterinary and Life Sciences > Institute of Biodiversity Animal Health and Comparative Medicine
College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:28 September 2016
Copyright Holders:Copyright © 2016 The Authors
First Published:First published in Journal of Organic Chemistry 81(20):9810-9819
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/K503058/1VICE PRINCIPAL RESEARCH & ENTERPRISE
554791EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VICE PRINCIPAL RESEARCH & ENTERPRISE